Episode 49: Riley Weston on always making time for the business side of the music

As a singer/songwriter, Riley Riley cut her first single, If I Said Howdy to You, after self-teaching herself the guitar in only 18 months. And while working on her debut album, Surrender Laughing, Riley had the opportunity to open for her long time musical heroes, Montgomery Gentry.

As an actress, Riley starred in the indie feature, Footprints, where she played a disturbed runaway in Hollywood who dresses up as Super Girl. Footprints was declared “one of the 10 Best Films so Far this Year” by the Chairman of the NY Film Critics Circle. Riley also starred in the hit TV movie, What About Your Friends.

As a writer, Riley has written for the WB television drama, Felicity as well as starred as Story Zimmer in the show. Riley also wrote and starred in the highly-rated ABC television movie, Christmas at Water’s Edge. Riley went on to write the hit TV movie, The Nanny Express, for Hallmark. The movie aired as the 2nd highest-rated movie for the network. Most recently, Riley’s latest TV movie, DAMAGED, premiered in January 2015 on the Lifetime network.

Table of Contents

10:40 – If you had to describe yourself as a band, song, or genre, what would it be?

12:12 – How did you get started in the music business?

26:44 – Looking back at your career, what stands out to you as your proudest moment?

37:00 – What’s been one of your biggest failures, and what lessons did you learn from that moving forward?

41:42 – Three things artists should be doing today to grow their fan-base and move their careers forward

If you had to describe yourself as a band, song, or genre, what would it be?

Country music! Not so much of the newer, not so country music. Country music because it tells you like it is, they don’t sugar coat it. It’s just brutally true and out there.

How did you get started in the music business?

I knew from a very young age that I wanted to be on a stage somewhere. I didn’t know what kind of stage, or where, or what, but I knew that I wanted to be performing. So I’m from the world’s smallest town called Pleasant Valley. It’s a two traffic light kind of a town.

And I got lucky early on. I walked into an agents office in Los Angeles and said that I should be in commercials. When you are young, you don’t second guess yourself. The point is that sometimes you have to push on the right doors, and knock them down if you have too.

Looking back at your career, what stands out to you as your proudest moment?

Almost every day I get to write a song that I’m excited about. If I had to pick one, I would say opening for Montgomery Gentry. That was my proudest moment.

I had never played with a full band. I had never stood up playing the guitar. You know, around Nashville we always have our guitars on our laps. And I had never had a huge show like that [Editors note: You’ll have to listen to the show to find out how Riley hooked up that particular gig].

What’s been one of your biggest failures, and what lessons did you learn from that moving forward?

I’ll tell you what, and this is gonna sound silly, but I don’t consider anything a failure. I’ve learned from every single experience. I’m not saying that I’m invincible. And I’m not saying that I do everything right, by any means. But all those little things [that I’ve done wrong], I wouldn’t do them again. So I’ve learned from it, and I can’t say that I’ve failed.

Three things artists should be doing today to grow their fan-base and move their careers forward:

First, get on social media. I despise it. It makes me want to vomit. Usually, on a daily basis, I hate wasting time “on the computer” doing stuff like this or on my phone. However, and that’s a big however, it’s sad to think that labels and publishers and producers look at that and want to see an engaged artist with a strong following.

Second, get a good website. This is an area where I followed my own advice. It’s expensive. But there are also ones you can find that you can do on your on now and they are very affordable.

Third, connect with you fans. It could be a contest here or there, or giving away a free song. Are you changing your CD every single year? Are you posting Youtube? Again, it comes back to social media here.